Synthesis of 3,5-disubstituted 1,2,4-oxadiazoles using ionic liquid-phase organic synthesis (IoLiPOS) methodology - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Tetrahedron Année : 2010

Synthesis of 3,5-disubstituted 1,2,4-oxadiazoles using ionic liquid-phase organic synthesis (IoLiPOS) methodology

Résumé

New 3,5-disubstituted 1,2,4-oxadiazoles were synthesized in five steps by ionic liquid-phase organic synthesis (IoLiPOS) methodology. The strategy involved the preparation of amidoxime from the ionic liquid-phase bound arylnitrile. Addition of various carboxylic acid to the amidoxime produced the expected 3,5-disubstituted 1,2,4-oxadiazoles via the stable O-acyl amidoxime intermediate grafted on the ionic liquid-phase. The 1,2,4-oxadiazoles were easily cleaved by transesterification under mild reaction conditions in high purity with good overall yields. The structures of the intermediates in each step were verified by routine spectroscopic analysis (1H, 13C NMR, and HRMS).

Domaines

Chimie organique

Dates et versions

hal-00869781 , version 1 (04-10-2013)

Identifiants

Citer

Laetitia Duchet, Jean-Christophe Legeay, Daniel Carrié, Ludovic Paquin, Jean-Jacques Vanden, et al.. Synthesis of 3,5-disubstituted 1,2,4-oxadiazoles using ionic liquid-phase organic synthesis (IoLiPOS) methodology. Tetrahedron, 2010, 66 (4), pp.986-994. ⟨10.1016/j.tet.2009.11.079⟩. ⟨hal-00869781⟩
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